


The Firsts

by thefriendlymushroom



Series: Supernatural Imagines [6]
Category: Supernatural
Genre: F/M, First Kiss, First Meetings, Firsts, Fluff, Meeting the Parents, Other, POV Second Person, taken from a prompt list
Language: English
Status: In-Progress
Published: 2017-09-17
Updated: 2018-07-01
Packaged: 2018-12-31 01:19:17
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,454
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12121419
Author URL: https://archiveofourown.org/users/thefriendlymushroom/pseuds/thefriendlymushroom
Summary: Series of non-chronological oneshots of firsts between Dean and the reader, from the first time meeting to the first death.





	1. The First Time Meeting

**Author's Note:**

> Prompt list found [here](https://kaylaxwrites.tumblr.com/post/154974245293/avengersfictionxreader-i-made-my-own-prompt)

**Notes for the Chapter:**

> [prompt list](https://kaylaxwrites.tumblr.com/post/154974245293/avengersfictionxreader-i-made-my-own-prompt)

The first time you met Dean Winchester, you hated him. You absolutely _despised_ him. There were no words for the loathing you had for the man.

You were on your first major solo hunt—a werewolf case—when Dean just had to swoop in and take over your case.

Under the guise of a federal agent, you had snuck into the morgue to examine the body. The coroner was reading you details off the autopsy report when the Winchesters swaggered into the room. They immediately flashed their federal IDs at the coroner and you sighed in relief: their IDs were incredibly realistic, but your training immediately allowed you to recognize them as fakes. _Other hunters_ , your mind supplied.

“Thank you, uh, Agent Lee,” the shorter of the two had said, reading your name off the nametag the morgue had given you upon signing in, “but I think we can handle it from here.”

“You know these men?” the coroner asked you.

You opened your mouth to speak, but the stranger cut you off. “We’re her superiors. Sent her ahead to get a lay of the land.” He even had the nerve to look over and _wink_ at you. “Agent Banner, nice to meet you,” he said, shaking the coroner’s hand.

The taller of the two men joined the coroner and “Agent Banner” at the table. You were clearly dismissed. You resisted the urge to huff and stomp out of the room. You decided to wait and pout at your car instead.

It was over half an hour before the two “agents” walked out of the building. You leaned off your car as they approached. “Are you trying to take my case?” you hissed at them as they got into ear shot.

“Ma’am, this is a federal investigation,” the shorter one began.

You rolled your eyes. “Oh, cut the crap. I know you’re hunters. Now _why_ are you stealing my case?”

“Leave this one to the professionals, sweetheart. Go back to your books and research—don’t want you getting hurt now.” He spun on his heal and headed for his car. The taller man was left standing behind, running a hand through his hair.

“Is he always such a dick?” you asked.

The stranger chuckled. “He’s not usually this bad. We had a long car ride. He’s grumpy.” He paused. “Name’s Sam Winchester, by the way. That’s my brother, Dean.”

You raised an eyebrow. “Winchester, huh?”

“Yeah… Listen, no matter my brother says, we could use whatever info you have—” A car horn blared. “Meet me at the pub on 6th street later tonight. If we work together, the faster this thing will be killed.” With a wave, he jogged off to his brother’s shiny black car.

When you met the Winchester later in the day, Dean was a little bit more tolerable, and his added charm reduced your anger by the second. At the pub, the younger brother had already saved a table and was heavily focused on whatever was on his laptop. You scoped out the rest of the bar and spotted Dean hitting on the bartender. You turned and walked to Sam. He looked up at you as you sat across from him. “Hey, you made it,” he said. He immediately started explaining all the information he’d found. “So, get this…”

The two of you compared notes until Dean barged in a few minutes later, sliding a shot across the table to you. “Not even going to have a few drinks first, Sammy?” Sam rolled his eyes, but accepted the beer his brother handed him.

Dean didn’t talk to you very much after introducing himself. He spent his time pretending to research with you and Sam, hustling pool, and flirting with all the girls he came across. You winced as he made a cringe-worthy pass at a group of girls at a bachelorette party. You mostly tried to ignore him, but, somehow, he still grated your last nerve from all the way across room.

Despite your irritation at the Winchesters part way taking over your case, you had to admit you worked well with them—well, Sam, anyway. By the end of the night, you had pinpointed the location of where the werewolf lived. You and Sam planned to meet up the next day and the three of you would hopefully take down this wolf.

* * *

You parked your car down the block from the run-down house the werewolf was holed up in. You were checking your weapons and counting your bullets as the Winchesters did the same. You ran over the plan: “One of the boards in the back window got knocked in, so I’ll crawl through there and let you guys in the front. If all’s according to plan, he should be sleeping in the upstairs bedroom. If not, well…we’ll see how it goes.”

“You sure you can handle it, sweetheart?” Dean asked you. You scoffed, and walked away as Dean and Sam hid behind the tree line as you snuck up to the house. The window was higher up than you expected, so it was a bit difficult to wiggle in between the slats of the window. You winced when you made more noise than intended on landing. You paused and listened intently, to see if the werewolf had noticed. With no noise from the rest of the house, you continued on.

You were on the final stretch of making it to the front door when you were suddenly tackled from behind. You yelped as your palms and knees were skinned as you slid across the floor. Before you could react, the werewolf was on top of you. You felt his extended nails dig into your flesh, nearly breaking skin. You could hear his jaws snapping by your ear. This was so not good. Your mind ran through a slew of curses as you struggled your way from the werewolf’s grip.

A heel went up and nailed the wolf directly between the legs, granting you a moment of freedom. Rolling onto your back in a pose worthy of an action movie, you fired off three shots of silver bullets. The first missed. The second lodged itself in the werewolf’s shoulder. The third hit its mark dead in the center of the werewolf’s chest. The wolf slumped anticlimactically on the floor.

You laid there for a few moments, breathless, before the pounding on the front door registered in your senses. Groaning, you stood and opened the door to find Sam on his knees, in the middle of picking the lock. They quickly stepped through the door, alert, and ready to shoot the first thing that moved. They were surprised to find no threat. Channeling your inner Vanna White, you threw your arms out, “jazz-handsing” towards the corpse on the floor. “Ta-da!”

“Nice shot,” Sam complimented, but quickly passed you to scope the rest of the house.

You turned to Dean. “Looks like I was able to handle it, _sweetheart_.”

“Let’s see you do it again,” he replied, following his brother.

You resisted the urge to stomp you foot. This man was _impossible._


	2. The First Kiss

Dean answered your call on the third ring. “What’s goin’ on, princess?” he greeted. Your rolled your eyes at the pet name.

  
Shuffling the papers in front of you, you replied, “I need help on a hunt.”

  
“Thought you could handle these things on your own.”

Were you ever going to live that down? Since first meeting, you had crossed paths with the Winchesters several times—you always arrived at the same hunts. You were have convinced they were stalking you. “Yeah, well, not this time. It’s a wendigo. At least, I’m pretty sure it is…”

“Say no more. Text me where you are and we’ll be there ASAP.”

“Thanks, Dean.”

You hung up and sighed. It was time to dig back into the research—your least favorite aspect about your occupation.

Dean managed to the make the drive in eighteen hours, a feat you were pretty impressed with. After checking themselves into a motel room in the same building, the brothers joined you in your room. You explained them all your research—how people, couples, families, had all gone missing out of the state park on camping visits. The pattern cycled itself every seventeen years, always taking the same amount of people, and always disappearing without a trace. You glossed over interviews from survivors and evidence of the victims’ remains.

“So, I’m one hundred percent sure it’s a wendigo,” you concluded. “I just need help finding its lair and finishing it off and then we’ll be good to go.”

“Have you narrowed down locations?” Sam asked, looking over your papers.

You pulled a map from under the town’s encyclopedia you borrowed from the library. “Yeah. There’s an old abandoned train track that runs through the center of the park. Locals say there’s a collapsed tunnel towards the east, so it may be there, but then there’s any number of bear caves it could be hiding in.” You pulled out a pink highlighter and circled an area on the map, mostly containing the old rail lines. “All the disappearances happened in this vicinity. So, we’re going to start there.”

Dean stood from his chair at the kitchen table and clapped loudly. “Sounds like a plan,” he said, swinging his jacket over his shoulders. “We’ll meet up in the morning and gank this son of a bitch tomorrow.” Halfway out the door, he turned to you. “Kayla, know the best bars in this place?” You pointed left, and he took off.

You looked at Sam, who was still reading up on the local history. “Your brother’s an alcoholic.” Sam just shrugged.

* * *

 

You woke up bright and early the next morning, eager to move away from this crappy motel and on to the next. You and Sam stood next to the Impala, gear all packed, waiting for Dean to mosey his way on out. “It’s too goddamn early,” he groaned, climbing into the driver’s seat. He grumbled for a few moments before you handed him a coffee and a donut you managed to grab before the boys were awake. He shut up after that.  
Twenty minutes later, you pulled up to the park’s parking lot. One woman packed her dog into the car after an early morning hike and drove off. You were thankful you were now the only ones in the lot. What would civilians think about you unloading a flamethrower from the trunk of the car?

Bags slung over your shoulders, you and the Winchesters began hiking up a well-worn trail. Sam was your GPS for this mission, as you were shit at giving directions with no landmarks around. He directed you up and over a hill before moving away from the marked trail. You were hot and sweaty by the time you hiked to the top of the mountain nearly an hour and a half later. From this vantage point, you could see the area around you perfectly. You spotted the collapsed rail tunnel and two or three caves dotted on the surrounding mountainsides.

Sam pulled walkie talkies out of his bag and handed you and Dean one each. “We have three main points of interest—the tunnel, a cave a mile to the north, and an abandoned mine three quarters of a mile west of here. So we’ll split up, but walkie at the first sign of anything suspicious.” The three of you drew straws to see who would go where. You ended up with the cave. It was the least likely, and therefore the least exciting option. Less chance of death, though, your mind reminded you and internally scoffed at yourself.

Fifteen minutes later, you began noticing suspicious signs. You first saw trash littered about, but didn’t think much of it. Some hikers are just messy, you guessed. Then you noticed an abandoned camp fire—not warm in the slightest but recent enough. Then came the fabric scraps attached to tree limbs and bush thorns. Then splatters of blood on the creek bed. Carefully pulling out your flare gun, you radioed Sam and Dean. “Think it’s this way guys,” you muttered. But who were kidding—it didn’t matter how quiet you were. If this thing was awake, it’d have you pinpointed immediately. “There’s blood trails.”

“On my way,” replied Dean.

Sam spoke next. “There’s nothing at the mine. Stay where you are, Kayla!”

You firmly intended on staying rooted to your spot until you heard the cries of agony. Shit. Wendigos were excellent mimickers—but what if this was actually a person? You had to do something. “There’s screams,” you said into the walkie talkie. “I’m—” Then Sam and Dean heard nothing but static.

* * *

 

You weren’t sure how long you were out, but you awoke to your heartbeat banging against the side of your skull. You heard voices—or was it only one?—but they were muffled by the ringing in your ears and you couldn’t make out what they were saying. You pretended to still be unconscious while you took stock of your body.

The left side of your rib cage was throbbing. You felt blood trickle down the side of your face. Wrists were bound. You could only stand on tip toe to reach the ground, but the rock wall behind you was angled enough that you were somewhat draped against it, relieving the strain from your wrists and shoulders, albeit infinitesimally.

Finally, you registered the voice speaking to you. “Please be alive, please be alive.” It was a woman. She repeated her phrase like a mantra. You groaned and rotated you neck a little bit. “Oh thank god,” the woman sighed in relief. You opened your eyes to see the woman about five feet away from you, restrained in a similar fashion. There was a man next to her and you could tell from here he was already dead.

“Hi,” you croaked. Your mouth was dry and your throat hoarse. “What’s your name?”

“Sarah.”

“I’m Y/N. I’m here to rescue you.”

“Oh.”

You chuckled a little, then winced at the pain it caused in your ribs. At least one was broken, you gathered. “I know, not doing a good job of it.”

“What the fuck is this thing, that has us?”

“You up to date on folklore and cryptids?” She nodded. “It’s a wendigo. A big, scary, cannibalistic monster that likes to stock up on human bodies for the winter.”

“Shit, those are real?” Her voice was laced with panic. Fuck, don’t freak out on me here, you thought.

“Um…yeah. Unfortunately.” Her breathing picked up pace. “Listen, I need you to calm down. It’s the only way we’re going to make it out of here.”

Sarah took big, large, forceful breaths. “Yeah. Stay calm. Stay calm.” But her deep breathing and phrase repetitions clearly weren’t working.

You took the time now to assess your surroundings. It was dark, but some sunlight was filtering through somewhere so it wasn’t pitch black. The ropes around your wrists were tight, but you’ve escaped from tighter bonds. With a little working, you could get them loose. You could make out decomposing bodies around you, but you were thankful your mind hadn’t taken the time to register the smell just yet. The alcove you were in had only one way out and you hoped the monster was out chasing the Winchesters, leaving you enough time to bring Sarah to safety.

Moments later, after nearly dislocating a joint or two, you were out of the bonds. You landed on the floor heavily. Your feet couldn’t take the weight and your head throbbed louder, forcing you to slide to the ground. You were definitely going to feel this in the morning. Pushing your own pain aside, you stood to free Sarah. She had to have been here for two days, maybe more, and you knew you had to get her out of here. Once free, she leaned heavily against you. It took everything you had to keep the both of you upright.

You shuffled along the ground to see what supplies might have been dropped that the wendigo didn’t take. A gun, anything… You found nothing in the dark. We’re going to have to make this escape quick, then.  
It was a few minutes of navigating the dark twist and turns of the cave before you heard noise. Sarah questioned you, but you quickly hushed her. Not that it would make much of a difference, anyway.

“Kayla, duck!” was the next sound you heard and you reacted instinctively, grabbing Sarah by the waist and dragging her to the ground. The bright light of a flare gun blinded you and you heard the screeching of the wendigo. Sam and Dean fired three more shots into the beast until it finally crumbled.

“You guys okay?” Sam asked, shining the flashlight on the crumpled heap you and Sarah made on the ground.

“Peachy,” you answered. “Guys, this is Sarah.” You pushed her to standing, where Sam picked her up. Dean pulled you up and supported the majority of your weight. Sam tried to make small talk with Sarah as the four of you walked to the Impala. This was going to be a long walk.

It was nearing sunset as you finally reached the Impala. You dropped Sarah off at a hospital, leaving her with a cover story of being attacked by a bear and your phone numbers, before returning the motel.

Upon arrival, you immediately broke out the liquor, taking a few swigs as your pulled your top off and sat on the bed. “Stitch me up,” you said, voice full of fake bravado. You poured the liquor down your side, hissing, as Dean prepped the first aid kit you had brought.

“You ready for this?” Dean asked you, pulling a chair to the bed next to you.

“No,” you replied. Dean held the needle and sutures near your skin. He took a breath to steady himself. Then the needle pierced your skin. You cried out. Then it happened again. And again. And again. And again. And again. Twenty-four stitches in total. A new record for you. Dean helped you sit up. You rested your forehead against his shoulder, out of breath from the pain.

“Y/N?” Dean said your name softly.

You slowly sat up to look at him. “Yeah?” He didn’t say anything for a while. You stared into each other’s eyes, getting lost in them. “Dean?”

Then his lips were on yours, softer than you expected.

He broke away, as quick as he was on you.

“I don’t think we should ever split up like that again,” he said quietly.

You would have agreed, but if it got you kisses every time, you weren’t so sure…


	3. The First "I Love You"

Throughout your entire relationship with Dean, you could count on one hand the number of times the eldest Winchester uttered the words "I love you." It didn't bother you much—it was just who Dean was, who most hunters are. Instead, you always looked for the subtle ways Dean professed his love: pulling you closer in the night, offering to share the last slice of pie, booting Sam to the backseat of the Impala to let you ride shotgun. In his everyday actions, it was obvious Dean Winchester loved you.

Though you adored these little moments, you cherished the verbal "I love you"s even more. The first of these would always be your favorite, as it was your little secret. Dean didn't know you knew of his first "I love you"—you were supposed to be asleep.

* * *

 

It was no secret that Dean had nightmares. It was no surprise, either. (What hunter  _didn't_ have nightmares?) The fact that you witness them was further testament to his love. It was one of these small acts of love that led to his first confession.

He was talking in his sleep that night, tossing and turning, and crying out your name. You knew this was the start of a nightmare and you knew where it could lead. To ease him a little, you rolled over and pulled him closer to yourself, nuzzling your head into his shoulder. He stilled then and sighed. You were almost asleep again when his nightmare returned. He woke up gasping for breath, but immediately froze for fear of waking you. You showed no sign that you were awake; he was sometimes embarrassed having witnesses to his nightmares, so you usually chose to let him calm down in peace. Dean's breathing steadied moments later and he turned to face you.

You thought he had drifted off again when he sighed into your hair. "Y/N?" he called softly. You didn't reply. You didn't move. Satisfied you couldn't hear him, Dean continued to speak. "I love you," he whispered. He paused. Minutes later, he said it again, as if he were in disbelief. "I love you."

With a smile on your face, you curled further into his chest.  _I love you, too,_ you thought.

That night, Dean slept better than he had in years. 


	4. Meeting the Parents

**Summary for the Chapter:**

> You meet Mary Winchester for the first time.

Being in the lifestyle you were, you never once thought you would have a "Meet the Parents" type of moment. It just didn't happen. Most hunters didn't have families. And those that did? Well, it wasn't like you ever stuck around long enough to get that close to a person anyway. The Winchesters were one of the few hunters you knew that had families and even then, it was always just the two of them against the world. Their parents had died years ago. But you should have realized that Winchesters didn't really tend to stay dead. 

So it was a hell of a surprise the night the boys brought Mary Winchester home.

* * *

 

You had been away from the bunker for a few weeks, helping out a friend of yours in West Virginia with a shapeshifter trying to pose as the Pt. Pleasant Mothman. Tricky case, that was. It was long and rough and you were just ready to go home and watch Netflix with Dean—you certainly weren't prepared to try and impress his mother.

"Dean?" you called out as you made your way down the bunker's staircase. "I'm back!" You dropped all of your belongings at the base of the stairwell and began peeling off your jacket. You froze and tensed when you caught sight of blonde hair that certainly didn't belong to either of the boys. You turned to stare at the woman casually sitting at the war room table. She also tensed. Clearly, she wasn't expecting you either. You wondered if you could reach the gun in your duffel before she pulled the one from under the table. You doubted it. "Where are Sam and Dean?" you asked.

She didn't give you an answer. Instead, she asked you a question in return. "Who are you?"

"I could be asking you the same thing, lady."

Before you could decide if you wanted to dive for a weapon, Sam and Dean entered the room. They were arguing over some dumb TV show, so they didn't immediately notice the tension in the room. Sam was the first to pay attention, however. "Hey-hey-hey, easy," he said, coming to stand between you and the blonde, noticing how ready you were to pounce.

"Care to tell me why there's a stranger in the bunker?" you said.

Sam shot a look over to Dean. "You didn't tell her??"

Dean raised his hands in defense. "I didn't exactly think this was something you could tell your girlfriend over the phone! 'Oh, yeah, Kayla, see you when you get back! Yeah, by the way, my mom's back from the dead—'"

You and the woman interrupted Dean simultaneously. "Girlfriend?" she exclaimed while you shouted, "This is your  _Mom_?"

Sam half smiled, half grimaced. "Mom, this is Dean's girlfriend, Kayla. Kayla, this is...our mom, Mary."

"Holy shit," you breathed. Suddenly, you worried if you looked presentable. This was  _not_ how you wanted to make a first impression—two week old jeans and an old, ratty sweatshirt? Definitely not how you would have wanted to meet the Winchester matriarch. "Dean, can I talk to you for a moment?" you said through slightly ground teeth. You drug him by the sleeve down the hall until you were out of earshot. "What the hell, Dean?" you whisper-shouted, letting Dean's arm go with a slight shove.

"What?"

"You didn't tell me your mom was alive and staying here?"

"I wanted to tell you in person!"

"Maybe you should have stopped to tell me  _before_ I almost pulled a gun on your  _mom_?"

Dean laughed a little. "You weren't gonna—"

"I thought she broke in!" You ran your hands through your hair. "Oh my god I almost pulled a  _gun_ on your mom," you said somewhat frantically. "She's gonna hate me, oh my god. I needed to make a good first impression!" You were a hair away from panicking now. "I should go apologize—but not in this." You hurried away from Dean to your bedroom. You first impression was already made, but maybe the second could be made better with  some nice jeans and a good top.

Ten minutes later, you found Mary in the kitchen. You slowly stepped into  the room. She was making coffee. "Mary? Ah—Mrs. Winchester?"

She turned and smiled at you. "Mary's fine." She pulled two mugs from the cabinet and filled them each with coffee. She offered one to you and made her way to sit at the table. You followed her there, mug in hand.

"I, uh, I'm sorry for earlier. I wasn't expecting anyone, let alone..."

"Your boyfriend's dead mother?"

You chuckled. "Yeah."

"It's okay. I'm happy to see you were willing to protect my boys and their home."

"Not gonna lie, they make it difficult sometimes," you laughed. "They collect too many enemies, it seems."

"Hard not to in this line of work."

"I suppose so."

You sat in silence for a few moments, each of you slowly sipping at your coffees. Mary was the one to break the silence. "What are they like?" she asked. 

You smiled. "Usually? A pain in the ass."

* * *

 

Sam and Dead found the two of you there in the kitchen hours later. You were knee-deep in embarrassing stories—stories the boys weren't sure they wanted their mother to know, but stories you told her anyway. They eventually joined in on the conversation, eager to argue their version of things. The rest of the night was filled with laughter and joy and you were happy to have met Mary Winchester—even if it didn't go as you would have planned.

**Notes for the Chapter:**

> Ahhh I suck at wrapping chapters up, but I hope you liked it! Leave a comment and/or hit me up @kaylaxwrites on tumblr. Y'all are great ily


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